Top 14 movies every aspiring entrepreneur should watch

Books, movies and TV shows are filled with incredible stories that can help guide and mentor business owners, CEOs and aspiring entrepreneurs. Unlike business seminars and conferences, movies offers a learning experience that allows you to take in valuable business advice from the comfort of your couch in your own time.

Here is our pick of top 12 movies every inspiring entrepreneur should watch. Please note, the descriptions below may contain spoilers.

14. The Great Gatsby

Leonardo DiCaprio and Tobey Maguire star in the film adaptation of F. Scott Fitzgerald’s 1985 novel with the same name. Everything in this movie is big and lavish, with exorbitant amounts of money splashed around. Nick Carraway moves into a small house next to the mansion of Gatsby, a very rich and mysterious character who throws the most extravagant parties. Gatsby’s story teaches us what it means to seize an opportunity – “fake it till you make it”, and to get your priorities in order. Most importantly, it demonstrates the power of hope.

13. Walt before Mickey

The 2015 biographical drama follows the early days of Walt Disney. From beginning to end, this movie is filled with lessons and hope for entrepreneurs. It is a true rags-to-riches tale highlighting the numerous times Disney failed before finally becoming the man behind the mouse. Employees walked out on him, he had to swallow his pride (more than once), he was betrayed, lost everything (more than once), and even spent some time living on the street. This is a must-watch movie for any aspiring entrepreneur.

12. Waffle Street

One Tree Hill fans would be delighted to see James Lafferty back in front of the camera. In Waffle Street, James portrays the character James Adams, a financial guru who loses his hedge fund job and ends up serving tables at a popular chicken and waffle restaurant. The movie has one very important lesson: nothing pays better than hard work.

11. Julie & Julia

This story, based on true events, looks at the lives of two “average” women doing not so average things. Julia Child overcame multiple impediments to become one of the biggest culinary names in the world. In 2002, Julie Powell found herself almost 30 and stuck in a brain dead job. She decides to challenge herself by cooking all the recipes in Julia’s first cookbook. This movie is a great inspiration for all generations, proving once again that it is never too late to bake your dream cake, and eat it too.

10. Burnt

This movie starring Bradley Cooper did not get the best reviews, so if you’re a serious movie critic, don’t expect Oscar-worthy performances. Nonetheless, I do think it’s a must-watch movie for aspiring entrepreneurs who are considering a business venture in the food or hospitality industry.

Cooper plays a chef with a dodgy past who is trying to clean up his act by heading a restaurant with the potential to get three Michelin stars.

The movie gives a very honest look into the gruelling work and cruel hours required to run a business where your core job is to cater to other people’s culinary needs.

9. Glengarry Glen Ross

This is probably the most cliché entry on this list, but it made the list for good reason. Glengarry Glen Ross is a 1992 classic that follows two intense days in the lives of four real estate salesmen who are battling it out for the two sales positions remaining at their real estate firm.

This movie has some interesting lessons for entrepreneurs about sales techniques and customer relations.

8. The Boss

This movie is a little on the lighter side. If you’re not a Melissa McCarthy fan (I can’t imagine why), then this movie is not for you. McCarthy plays a successful business owner who just finished a prison sentence for tax evasion. On her release she moves in with her ex assistant. It’s here where she finds her next big venture.

The Boss has great lessons about finding opportunities and teamwork all wrapped up in lots of laughter.

7. Erin Brockovich

You’ve probably seen this movie on lists like this before. If you haven’t watched it yet, you are missing out on a lot of vital entrepreneurship lessons.

Erin Brockovich is based on the true-life story of a struggling mother trying everything to provide for her family. She ends up saving not only her family, but an entire community.

Erin Brockovich reminds entrepreneurs that spotting an opportunity is only the first step to success. Hard work, dedication and sacrifice are all part of the journey.

6. Spotlight

Spotlight is not a movie about entrepreneurship or running a business per se. The movie, based on true events, focuses on a group of journalists unravelling a rather sensitive story that involves politics, lawyers and religion.

One of the biggest challenges of starting your own business is looking past those who believe you will fail. They don’t have to tell you to your face that they don’t believe in you – sometimes all it takes is a condescending look or smile.

Starting your own business is almost like coming out as gay – some people are going to admire your courage while others are going to think it is just a phase. The journalists in Spotlight are about to write a story that no-one wants to hear, and you can definitely learn a thing or two from them about swimming upstream.

5. Zootopia

Even if you are a bigshot CEO, you should never underestimate the influence animation movies can have on your entrepreneurial thinking.

Zootopia is a movie with as much to teach adults as it does to kids. It features Judy Hopps, a rabbit from Bunnyborrow, who moves to the big city to become the first bunny cop in the history of Zootopia. I am sure you can imagine where this is going.

The story is as powerful as it is witty. Do yourself a favour and take a break from all the “adulting” you’ve been doing by watching this movie. You’d be surprised at how refreshing and inspiring it can be.

4. The Intern

In The Intern, Robert De Niro’s character is a retired mature man who takes up an intern position at a tech company.

The Intern was, surprisingly, filled with loads of valuable reminders of what it takes to be an entrepreneur in the 21st century. De Niro’s boss, played by Anne Hathaway, faces the oftentimes heart-breaking reality of making sacrifices in the name of your business, while her much older intern is bringing true work ethic back in style.

3. Joy

Joy is the second movie on this list based on the true-life story of a strong, determined woman. Jennifer Lawrens portrays the story of Joy Mangano, the inventor and entrepreneur whose career started with the Miracle Mop.

Joy was told numerous times that her household cleaning product was not worth any attention, and that she didn’t have what it takes to turn her idea into a business. Not to giveaway too many spoilers, but today Joy Mangano has a net worth of $50 million.

2. Jobs / Steve Jobs / The Social Network / Pirates of Silicon Valley

Okay, so these are technical four different movies, but due to their similar focus, I decided to group them together as one.

Jobs (Ashton Kutcher), Steve Jobs (Michael Fassbender), The Social Network (Jesse Eisenberg) and Pirates of Silicon Valley (Noah Wyle) are four incredible movies that focus on the lives and careers of Silicon Valley’s biggest tech entrepreneurs.

All four of these movies give you a peek into what it will take to be the next Steve Jobs, Mark Zuckerberg or Bill Gates of your industry. Although their career paths and obstacles were very different, there is clearly a common mindset, determination and work ethic that can be found in all three these tech giants.

1. Eddie the Eagle

Sports movies always make for great motivational films, and as far as I’m concerned Eddie the Eagle is right up there with Moneyball and Jerry Maguire.

All Eddie wants to do is participate in the Olympic Games. Throughout his life every decision Eddie makes, he makes with this goal in mind. He understands that following your dreams means taking risks and ignoring naysayers. Most importantly, Eddie understands that if one strategy doesn’t work, it doesn’t mean you have to give up on your dream, it just means you need to change your strategy.

This movie is heartfelt, funny and will definitely inspire you to keep going.

About The Author

Enrique is the eternal entrepreneur: his first venture was selling off his parents’ household goods at bargain prices to their neighbours at age seven. All other endeavours thus far have been entirely above board.